One of the best things about the world of technology is that you can end up in it having come from any direction. The most successful founders, venture capitalists, designers, etc. have fascinating stories behind their success, and every week Charming Robot‘s Dan Maccarone sits down over our guest’s favorite cocktail, wine or beer to hear where they came from and what they’ve learned along the way.

Arikia Millikan is a journalist and entrepreneur with a resume that boasts digitizing traditionally print-centric brands. It’s a career that’s given her a fair share of behind-the-scenes experiences with the epidemic that’s overtaking the industry – the continued and steepening uphill battle of maintaining the right motivation in the world of news and content. Over Bloody Marys (with a fun twist) at Fools Gold in NYC, she explains how her unique approach in applying engineering principles paired with a “squeaky wheel” reputation help her press forward and innovate within this challenging space.

Topics we discuss include:

*Me being dragged kicking and screaming into learning about journalism business models.

*Why Medium is the worst.

*How I tried to help several print-centric media companies monetize their online content before that was cool and nobody listened to me, even though I was ultimately correct.

In this issue, we speak with Cyber Communication Specialist Arikia Millikan, about why she started using digital security and privacy tools as a journalist and her recent efforts hosting CryptoParty workshops to teach people how to develop personal risk assessments and how to make use of increasingly broad-based and user-friendly tools to defend themselves.

Last week, journalist Arikia Millikan reached out to women-in-tech listservs with some basic pointers on things like encryption, warning that “now is a good time to get serious about online security.” The response was strong enough that she followed up on Sunday with what’s known as a cryptoparty, where just under a dozen people gathered to learn more about protecting their online privacy. They went over security best practices and swapped “keys” — a phrase that has nothing to do with swinging and everything to do with vouching for the authenticity of each others’ encrypted accounts. The gender ratio was evenly split, which is rare for these kinds of events, she said.